Articles producció científica> Química Física i Inorgànica

Phosphite-Thiother Ligands Derived from Carbohydrates allow the Enantioswitchable Hydrogenation of Cyclic ¿-Enamides by using either Rh or Ir Catalysts

  • Dades identificatives

    Identificador: imarina:3658373
    Autors:
    Margalef J, Pàmies O, Diéguez M
    Resum:
    Phosphite-thioether ligands with a simple modular architecture, derived from inexpensive l-(+)-tartaric acid and d-mannitol, have been for the first time successfully applied (ee values up to 99 %) in the synthesis of 2-aminotetralines and 3-aminochromanes by metal-catalyzed asymmetric hydrogenation of cyclic ¿-enamides. The ligands have the advantages of the robustness of the thioether/phosphite moieties and the extra control provided by the flexibility of the chiral pocket through the presence of a biaryl phosphite group and a modular carbohydrate-derived backbone. Moreover, they are solid and stable to air and they are therefore easy to handle, manipulate, and store. Usefully, both enantiomers of the hydrogenated products were obtained by simply switching from Rh to Ir. Low hydrogen pressure and environmentally friendly propylene carbonate can be used, with no loss of selectivity.
  • Altres:

    Autor segons l'article: Margalef J, Pàmies O, Diéguez M
    Departament: Química Física i Inorgànica Química Física i Inorgànica
    e-ISSN: 1521-3765
    Autor/s de la URV: Diéguez Fernández, Montserrat / Pamies Ollé, Oscar
    Paraules clau: Rhodium Phosphite-thioether ligands Iridium Cyclic ¿-enamides Cyclic ?-enamides Asymmetric hydrogenation phosphite-thioether ligands iridium cyclic ?-enamides asymmetric hydrogenation
    Resum: Phosphite-thioether ligands with a simple modular architecture, derived from inexpensive l-(+)-tartaric acid and d-mannitol, have been for the first time successfully applied (ee values up to 99 %) in the synthesis of 2-aminotetralines and 3-aminochromanes by metal-catalyzed asymmetric hydrogenation of cyclic ¿-enamides. The ligands have the advantages of the robustness of the thioether/phosphite moieties and the extra control provided by the flexibility of the chiral pocket through the presence of a biaryl phosphite group and a modular carbohydrate-derived backbone. Moreover, they are solid and stable to air and they are therefore easy to handle, manipulate, and store. Usefully, both enantiomers of the hydrogenated products were obtained by simply switching from Rh to Ir. Low hydrogen pressure and environmentally friendly propylene carbonate can be used, with no loss of selectivity.
    Grup de recerca: Organometàl·lics i Catàlisi Homogènia
    Àrees temàtiques: Química Organic chemistry Medicina i Materiais Interdisciplinar General medicine General chemistry Farmacia Engenharias iii Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências agrárias i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Biotecnología Biodiversidade Astronomia / física
    ISSN: 15213765
    Adreça de correu electrònic de l'autor: oscar.pamies@urv.cat montserrat.dieguez@urv.cat
    Identificador de l'autor: 0000-0002-2352-8508 0000-0002-8450-0656
    Pàgina final: 822
    Data d'alta del registre: 2024-09-07
    Volum de revista: 23
    Versió de l'article dipositat: info:eu-repo/semantics/acceptedVersion
    Enllaç font original: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201604483
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referència a l'article segons font original: Chemistry-A European Journal. 23 (4): 813-822
    Referència de l'ítem segons les normes APA: Margalef J, Pàmies O, Diéguez M (2017). Phosphite-Thiother Ligands Derived from Carbohydrates allow the Enantioswitchable Hydrogenation of Cyclic ¿-Enamides by using either Rh or Ir Catalysts. Chemistry-A European Journal, 23(4), 813-822. DOI: 10.1002/chem.201604483
    DOI de l'article: 10.1002/chem.201604483
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2017
    Pàgina inicial: 813
    Tipus de publicació: Journal Publications
  • Paraules clau:

    Catalysis,Chemistry,Chemistry (Miscellaneous),Chemistry, Multidisciplinary,Organic Chemistry
    Rhodium
    Phosphite-thioether ligands
    Iridium
    Cyclic ¿-enamides
    Cyclic ?-enamides
    Asymmetric hydrogenation
    phosphite-thioether ligands
    iridium
    cyclic ?-enamides
    asymmetric hydrogenation
    Química
    Organic chemistry
    Medicina i
    Materiais
    Interdisciplinar
    General medicine
    General chemistry
    Farmacia
    Engenharias iii
    Engenharias ii
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências biológicas i
    Ciências agrárias i
    Chemistry, multidisciplinary
    Chemistry (miscellaneous)
    Chemistry (all)
    Chemistry
    Catalysis
    Biotecnología
    Biodiversidade
    Astronomia / física
  • Documents:

  • Cerca a google

    Search to google scholar